Derpy Hooves gets less respect than Toad from the Mario universe. Assuming I was my OC, and assuming he was old enough to be a stallion(let's assume the human age of 21 in this case), that is the pony I would date. Also, first Derpy pick FTW.
I would date Luna or at less hangout with her since I'm a night person, I mean she dose deserve somepony to love her along with her night after doing her time on the moon and beside many girls out there will agreed that Night Time is the best setting for dating.
Well, hypothetically speaking, it would be either Twi or Tia. Leaning towards Tia a little, but not because she's an alicorn Princess. It's because she's so mysterious, I'd really like to get to know the mare behind that calm, alabaster mask she wears all the time. She must have been very lonely for a very long time and I know exactly how it feels like, so I can relate to that, since I have been lonely my entire life, seeking for my other half.